The further involvement of citizens in the processing of their own cases is attracting attention as a possible strategy for improving the quality of employment services across national borders. However, employment services are characterized by detailed regulation and strong elements of conditionality. This article utilizes Bernardo Zacka’s framework on morality at the street level, drawing on focus group interviews to analyze how caseworkers in Denmark experience and deal with such demands for increased client participation. (1) We map four normative considerations that are emphasized by our informants: legality, authenticity, realism, and resonance. (2) In doing so, we outline two central cross-pressures that arise as they strive to balance client participation with conditionality in practice, namely between legality and authenticity, on the one hand, and between realism and resonance, on the other hand. (3) Finally, we unfold three coping strategies pursued by caseworkers to dampen such tensions: dividing the self, dissolving contradictions, and disassembling clients’ wishes. We add to the literature by studying coping strategies from a perspective that carefully highlights the normative elements of employment service work—the values frontline workers attribute particular importance to and strive to actualize in their work.